CN102924496A - Method for preparing anti-bacterial compound - Google Patents
Method for preparing anti-bacterial compound Download PDFInfo
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- CN102924496A CN102924496A CN2012103775402A CN201210377540A CN102924496A CN 102924496 A CN102924496 A CN 102924496A CN 2012103775402 A CN2012103775402 A CN 2012103775402A CN 201210377540 A CN201210377540 A CN 201210377540A CN 102924496 A CN102924496 A CN 102924496A
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- antimicrobial compounds
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- tertiary amine
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Abstract
The invention is suitable for the technical field of organic synthesis, and provides a preparation method of an anti-bacterial compound. The method comprises the following steps of: preparing organo-silicone containing tertiary amine; and preparing an anti-bacterial compound. The preparation method of the compound has the advantages of simple process, easiness in controlling conditions and industrializing, and convenience in using in a wide range.
Description
The application's application number that to be the applicant submit on January 26th, 2010 is dividing an application of 201010116533.8 application for a patent for invention, by reference its full content is attached to the application.
Technical field
The invention belongs to technical field of organic synthesis, relate in particular to a kind of antimicrobial compounds preparation method
Background technology
Bacterium or fungi infestation have become the worldwide major issue that threatens human health and enjoy global medical and health care system to pay close attention to.Giving material or product surface anti-microbial property, stoping bacterium or fungi in its surface growth or breeding, even kill bacterium or the fungi on surface, is one of important means that solves bacterium or fungi infestation.Present international anti-biotic material can be divided into four large classes: (1) inorganic antiseptic, and such as nano titanium oxide, nanometer silver, Nanometer Copper, and their ion etc.(2) antiseptic-germicide is arranged, quaternary ammonium salt for example, thiazoles etc.; (3) polymer antibacterial agent, for example high molecular quaternary; (4) natural and modification antiseptic-germicide: such as chitosan, Sorbic Acid.
Give material or product surface anti-microbial property the most frequently used be the coating that contains antiseptic-germicide (such as nanometer silver, Nanometer Copper and their ion thereof or other antiseptic-germicides) at its surface-coated one deck, nanometer silver, Nanometer Copper and other heavy metals and heavy metal ion, rely on its slow release metal ions in surrounding environment and reach antibacterial or the sterilization purpose, yet the prolongation along with duration of service, its anti-microbial activity reduces gradually, until finally completely lose its anti-microbial activity, also may induce microbial variation simultaneously, increase the chemical sproof probability of generation.In addition, the hazardness of nano material also is familiar with by the mankind gradually and is paid close attention to.Its poor heat resistance of organic antibacterial agent and natural antibacterial agent has usually limited its use range.The high molecular quaternary antiseptic-germicide can overcome the shortcomings such as volatile, the difficult processing, poor chemical stability of small molecules antiseptic-germicide, and anti-microbial activity is good, is difficult for infiltrating through human body skin, thereby receives people's concern.[the Reactive of Fu Ruowen seminar for example; Functional polymers, 2007,67:355-366] prepared a series of methyl acrylic ester high molecular quaternary antiseptic-germicides, MIC is 1.56-20mg/mL.Polymkeric substance antiseptic-germicide main or polymkeric substance quaternary ammonium salt and polymkeric substance halogen amine antiseptic-germicide, its thermostability is also undesirable, and, in order to obtain good antiseptic-germicide, the general requirement antiseptic-germicide is water miscible, also there is leachability in these not immobilized polymer antibacterial agents and causes anti-microbial activity to lack persistence, equally also can cause certain pressure to surrounding environment.Such as the people such as Lowe [J. Appl.Polym. Sci., 2006,101:1036-1041] prepared a series of polymkeric substance trimethyl-glycine antiseptic-germicides, its minimum inhibitory concentration (MIC) is 1125-2000ug/mL, for the exploitation of antiseptic-germicide has proposed a kind of new thinking, can immobilized reactive functional groups but it does not have, keep away the shortcoming that unavoidable its release property runs off.
The antiseptic-germicide of this release property has the unfavorable factor of two aspects at least: the antiseptic-germicide that implant (1) has the ageing of release, and it is active to lack durable antibiotic; (2) antiseptic-germicide that discharges brings pressure to environment.These factors can not be ignored, and the antiseptic-germicide of the non-release property that exploitation and preparation are green is trend of the times.To be fixed in material or product surface with the chemical bond form with the anti-microbial activity group, it is active to give material or goods durable antibiotic, nor causes in to environment.Madkour [Langmuir, 2009,25:1060-1067] to be to contain the surface reaction of halosilanes and hydroxyl, further adopts the method for atom transfer radical polymerization to prepare the figure layer of quick antibacterial, but complex process, and condition is harsh, is difficult to industrialization.Saif [Langmuir, 2009,25:377-379] prepared the silicone Quaternary Ammonium Salt Antimicrobial Agent with durable antibiotic activity, and the DC-5700 out of early stage DOW Corning company research and development belongs to this class, but the thermotolerance of the antiseptic-germicide of quaternary ammonium salt is bad, thereby has limited its use range.
How to overcome the shortcoming that present antiseptic-germicide field exists as previously discussed, research and develop a class new can immobilizedly have the new demand that long-lasting antiseptic-germicide is human social development.
Summary of the invention
The object of the present invention is to provide a kind of antimicrobial compounds preparation method, prepared compound can pass through response type functional group (silicon alkoxyl group) with the chemical bonding mode securely with multiple material or Product Interface bonding, obtain lasting anti-microbial activity and wetting ability.
The organosilicon betaine type antimicrobial compounds that the present invention is prepared has general formula I:
Wherein, R
0=H, R
3X
R
1To be selected from-CH
3, or-CH
2CH
3
R
2To be selected from-OR
1,-CH
3, or-CH
2CH
3
R
3To be selected from-(CH
2)
p, p=1～10 wherein;
R
4Be-(CH
2)
qCH
3, wherein q=0～17, or R
4=H;
R
5Be-(CH
2)
qCH
3, wherein q=0～17, or R
5=H;
R
6To be selected from-(CH
2)
rNH (CH
2)
t, r wherein, t=1～10, or-(CH
2)
u, u=1～6 wherein;
Y be selected from-COO ,-SO
3
In the above-mentioned general formula I, substituent R
4With R
5Identical group or different groups.
The invention provides the preparation method of above-mentioned antimicrobial compounds, its synthesis technique is simple, and condition is easy to control, and productive rate is high, is easy to suitability for industrialized production.
This purpose is achieved in that a kind of preparation method of antimicrobial compounds, the steps include:
Produce the organo-siloxane that contains tertiary amine, and with this contain the organo-siloxane of tertiary amine and reactant B under agitation, in the environment of 10～80 ℃ of temperature sustained reaction 1～48h, get white sedimentable matter;
Above-mentioned white precipitate material is filtered or centrifugation, get organosilicon betaine type antimicrobial compounds, namely make target product;
Above-mentioned reactant B is to be selected from propane sultone, butyl sultone, vinylformic acid, β-propionic acid lactone, X (CH
2)
vSO
3 -, or X (CH
2)
vCO
2 -In a kind of, wherein X is Br, Cl or I, v is the positive integer more than or equal to 1.
Above-mentioned preparation method's typical synthetic route chart is:
In the above-mentioned preparation process, the preparation method who wherein contains the organo-siloxane of tertiary amine is: get (R
1O)
2R
2SiH and reactant A under 10 ~ 80 ℃ of temperature, under the effect of platinum group catalyst, carry out addition reaction of silicon with hydrogen, stir, and reaction duration 1 ~ 48h, and get final product; R wherein
1To be selected from-CH
3Or-CH
2CH
3, R
2To be selected from-OR
1,-CH
3Or-CH
2CH
3Reactant A is the alkene that contains tertiary amine, preferred DMAA or Diethyl Allylnime.
In the above-mentioned preparation process, wherein said platinum group catalyst is to be selected from chloroplatinic acid catalyst, SiO
2Loaded platinum catalyst, activated carbon supported type platinum catalyst or Karstedt type platinum catalyst.
In the above-mentioned preparation process, wherein contain tertiary amine organo-siloxane the preparation method also can for: get (R
1O)
2R
2SiR
3X and R
4R
5NH under 20 ~ 80 ℃ of temperature, adds the NaOH/ aqueous isopropanol as catalyzer, and under agitation reacts duration 2 ~ 48h, and get final product; Wherein, R
1Be-CH
3Or-CH
2CH
3R
2Be-OR
1,-CH
3Or-CH
2CH
3R
3To be selected from-(CH
2)
p, p=1～10 wherein; R
4Be-(CH
2)
qCH
3, q=0～17 wherein; R
5Be-(CH
2)
qCH
3, q=0～17 wherein; X is Br, Cl or I.
The present invention also provides the another kind of preparation method of above-mentioned antimicrobial compounds, the steps include:
To contain aminosiloxane and reactant B under agitation, in the environment of 10～80 ℃ of temperature sustained reaction 1～48h and organosilicon betaine type antimicrobial compounds, namely make target product
Similarly, above-mentioned reactant B is to be selected from propane sultone, butyl sultone, vinylformic acid, β-propionic acid lactone, X (CH
2)
vSO
3 -, or X (CH
2)
vCO
2 -In a kind of, wherein X is Br, Cl or I, v is the positive integer more than or equal to 1.
The advantage of technique scheme is: this antimicrobial compounds, have reactive functional groups---siloxanes, the chemical bonding effect can occur with the multiple material interface in it, thereby gives material or lasting anti-microbial activity and the very strong wetting ability of goods of being processed by antimicrobial compounds.Simultaneously, preparation method's synthesis technique is simple, and condition is controlled easily, is easy to industrialization, and using in broad range for it provides convenience.In addition, this antimicrobial compounds has also that particular advantages, the especially toxicity such as acid-and base-resisting, salt are low, chemical stability and Heat stability is good, and the various disinfection technologies that the product surface of processing through this antimicrobial compounds can stand to commonly use are processed.
Embodiment
In order to make purpose of the present invention, technical scheme and advantage clearer, below in conjunction with embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, is not intended to limit the present invention.
Embodiment 1
Take by weighing 98.6g triethoxyl silane [(CH
3CH
2O)
3SiH] join in the round-bottomed flask with mechanical stirring and reflux, after the Platinic chloride of adding 0.2ml/Isopropanol catalysis agent, under stirring and 60 ℃ of temperature, slowly drip 51.2g DMAA [CH with dropping funnel
2=CHCH
2N (CH
3)
2], dropwise rear continuation reaction 1h, cool to 50 ℃, then drip propane sultone [
, hereinafter to be referred as 1,3-PS] and 73.2g(is dissolved in the 400mL dehydrated alcohol), dropwise rear continuation reaction 1h, get white precipitation, centrifugation is purifying for several times, gets organosilicon sulfonate betaine antiseptic-germicide, and its structural formula is: (CH
3CH
2O)
3Si (CH
2)
3 +N (CH
3)
2(CH
2)
3SO
3 -, this antiseptic-germicide is 15mg/mL to the minimum inhibitory concentration (MIC) of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and minimum bactericidal concentration (MBC) is 20mg/mL.
Embodiment 2
Take by weighing 107.8g methyldiethoxysilane [(CH
3CH
2O)
2CH
3SiH] join in the Florence flask with magnetic agitation and reflux, add 0.25g SiO
2Behind the load type platinum Au catalyst, under magnetic agitation and 30 ℃ of temperature, slowly drip 88.9g Diethyl Allylnime [CH with dropping funnel
2=CHCH
2N (CH
2CH
3)
2], and beginning calculating reacting time, filtration under diminished pressure reclaims catalyzer behind the reaction 8h, then collect filtrate, and drip 1 of 97.6g in filtrate, 3-PS(is dissolved in the 400mL dehydrated alcohol), continue reaction 10h under 30 ℃ of temperature, white precipitation, filter and with washing with alcohol purifying for several times, get organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3CH
2O)
2SiCH
3(CH
2CH
2)
3 +N (CH
3)
2(CH
2)
3SO
3 -, this antiseptic-germicide is 25mg/mL to the MIC of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and MBC is 30mg/mL.
Embodiment 3
Take by weighing 107.6g methyldiethoxysilane [(CH
3CH
2O)
2CH
3SiH] join in the Florence flask with magnetic agitation and reflux, behind the Karstedt type platinum catalyst of adding 0.20g, under magnetic agitation He under 20 ℃ of temperature, slowly drip 68.2g DMAA [CH with dropping funnel
2=CHCH
2N (CH
3)
2], and the beginning calculating reacting time, filtration under diminished pressure reclaims catalyzer behind the reaction 24h, then collects filtrate, and drips 93.2 sodium chloroacetate [ClCH in filtrate
2CO
2Na] (being dissolved in the 400mL dehydrated alcohol), react 24h under 20 ℃ of temperature, get white precipitation, centrifugation is purifying for several times, gets organosilicon carboxylic acid type trimethyl-glycine antiseptic-germicide.Its structural formula is: (CH
3CH
2O)
2SiCH
3(CH
2)
3 +N (CH
3)
2CH
2CO
2 -, this antiseptic-germicide is 20mg/mL to the MIC of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and MBC is 25mg/mL.
Embodiment 4
Take by weighing 107.6g methyldiethoxysilane [(CH
3CH
2O)
2CH
3SiH] join in the round-bottomed flask with mechanical stirring and reflux, behind the activated carbon supported type platinum catalyst of adding 0.20g, under agitation with under 50 ℃ of temperature slowly drip 68.2g DMAA [CH with dropping funnel
2=CHCH
2N (CH
3)
2], dropwise rear continuation reaction 2h after filtration under diminished pressure reclaim catalyzer, then collect filtrate, and drip in the filtrate 57.7g beta-propiolactone [
] (being dissolved in the 400mL butanone), continue reaction 6h under 40 ℃ of temperature, get white precipitation, centrifugation is purifying for several times, gets organosilicon carboxylic acid type trimethyl-glycine antiseptic-germicide.Its structural formula is: (CH
3CH
2O)
2SiCH
3(CH
2)
3 +N (CH
3)
2(CH
2)
2CO
2 -, this antiseptic-germicide is 10mg/mL to the MIC of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and MBC is 20mg/mL.
Embodiment 5
Take by weighing 142.5g N.N-diethyl-3-aminopropyl trimethoxysilane [(CH
3CH
2)
2N (CH
2)
3Si (OCH
3)
3] join in the Florence flask with magnetic agitation and reflux, under magnetic agitation, slowly drip 1 of 73.2g, 3-PS(is dissolved in the 400mL acetone), behind 10 ℃ of reaction 48h, get white precipitation, centrifugation is purifying for several times, gets organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3O)
3Si (CH
2)
3 +N (CH
2CH
3)
2(CH
2)
3SO
3 -, this antiseptic-germicide is 15mg/mL to the MIC of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and MBC is 20mg/mL.
Embodiment 6
Get 97.8g Trimethoxy silane [HSi (OCH
3)
3] join in the Florence flask with mechanical stirring and reflux, behind the activated carbon supported type platinum catalyst of adding 0.20g, under magnetic agitation and 50 ℃ of temperature, slowly drip 88.9g Diethyl Allylnime [CH with dropping funnel
2=CHCH
2N (CH
2CH
3)
2], dropwising stopped heating behind the rear continuation reaction 2h, filtration under diminished pressure reclaims catalyzer, then collects filtrate, and drips the ClCH of 93.2g in the filtrate
2CH
2SO
3Na(is dissolved in the 400mL dehydrated alcohol), be heated to 50 ℃, continue reaction 10h, get white precipitation, filter and with absolute ethanol washing purifying for several times, get organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3O)
3Si (CH
2)
3 +N (CH
2CH
3)
2(CH
2)
2SO
3 -, this antiseptic-germicide is 20mg/mL to the MIC of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and MBC is 25mg/mL.
Embodiment 7
Take by weighing 124.0g N-(β-aminoethyl)-γ-aminopropyl methyl dimethoxysilane [NH
2(CH
2)
2NH (CH
2)
3SiCH
3(OCH
3)
2] join in the Florence flask with magnetic stirring apparatus and reflux, under magnetic agitation, slowly drip 1 of 73.2g, 3-PS(is dissolved in the 400mL dehydrated alcohol), be heated to 40 ℃ the reaction 2h after, get faint yellow oily thing organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3O)
3Si (CH
2)
3NH (CH
2)
2 +NH
2(CH
2)
3SO
3 -, this antiseptic-germicide is 25mg/mL to the MIC of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and MBC is 30mg/mL.
Embodiment 8
Take by weighing 119.2g r-chloropropyl trimethoxyl silane [(CH
3O)
3SiCH
2CH
2CH
2Cl] join in the round flask with mechanical stirrer and reflux, under agitation with under 80 ℃ of temperature slowly drip 60.7g di-n-propylamine [(CH with dropping funnel
3CH
2CH
2)
2NH] (being dissolved in the 200ml dehydrated alcohol), cool to 30 ℃ after dropwising rear continuation reaction 10h, drip 1 of 73.2g, 3-PS(is dissolved in the 200mL dehydrated alcohol), continue reaction 10h, get white precipitation, centrifugation is purifying for several times, get organosilicon sulfonate betaine antiseptic-germicide, its structural formula is: (CH
3O)
3Si (CH
2)
3 +N (CH
2CH
2CH
3)
2(CH
2)
3SO
3 -, this antiseptic-germicide is 15mg/mL to the minimum inhibitory concentration (MIC) of intestinal bacteria (8099) and streptococcus aureus (ATCC6538), and minimum bactericidal concentration (MBC) is 20mg/mL.
Above-mentioned example products therefrom is processed glass surface, all obtained contact angle and all be lower than the ultra-hydrophilic surface of 10 degree, and adopt colony counting method to test its anti-microbial activity and durable antibiotic activity, the result is as shown in table 1.
The durable antibiotic activation analysis (colony counting method) of the antiseptic-germicide of table 1 embodiment 1-8
In other preferred embodiment of the present invention, can select the CH with suitable amount of substance
3CH
2(CH
3O)
2SiH, CH
3CH
2(CH
3CH
2O)
2SiH, CH
3(CH
3O)
2SiH replaces (CH
3CH
2O)
3SiH or (CH
3O)
3SiH or (CH
3CH
2O)
2CH
3SiH; Also can select butyl sultone, vinylformic acid, X (CH with suitable amount of substance
2)
vSO
3Na or X (CH
2)
vCO
2Na(wherein X is Br, Cl or I; V is the positive integer more than or equal to 1) replace propane sultone, beta-propiolactone, ClCH
2CO
2Na or ClCH
2CH
2SO
3Na.
Above-described only is several embodiment of the present invention; it describes comparatively concrete and detailed; can not therefore be interpreted as the restriction to claim of the present invention; should be understood that; for the person of ordinary skill of the art; without departing from the inventive concept of the premise, can also make some other distortion and improvement, these all belong to protection scope of the present invention.
Claims (4)
1. an antimicrobial compounds preparation method the steps include:
Produce the organo-siloxane that contains tertiary amine, and with this contain the organo-siloxane of tertiary amine and reactant B under agitation, in the environment of 10～80 ℃ of temperature sustained reaction 1～48h, get white sedimentable matter;
Above-mentioned white precipitate material is filtered or the centrifugation purifying, get antimicrobial compounds, namely make target product; Above-mentioned reactant B is to be selected from propane sultone, butyl sultone, vinylformic acid, β-propionic acid lactone, X (CH
2)
vSO
3 -, or X (CH
2)
vCO
2 -In a kind of, wherein X is Br, Cl or I, v is the positive integer more than or equal to 1.
2. antimicrobial compounds preparation method according to claim 1 is characterized in that, the described preparation method who contains the organo-siloxane of tertiary amine is: get (R
1O)
2R
2SiH and reactant A under 10 ~ 80 ℃ of temperature, carry out addition reaction of silicon with hydrogen in the presence of platinum group catalyst, stir, and reaction duration 1 ~ 48h, and get final product; R wherein
1To be selected from-CH
3Or-CH
2CH
3, R
2To be selected from-OR
1,-CH
3Or-CH
2CH
3, described reactant A is selected from DMAA or Diethyl Allylnime.
3. antimicrobial compounds preparation method according to claim 2 is characterized in that, described platinum group catalyst is to be selected from chloroplatinic acid catalyst, SiO
2Loaded platinum catalyst, activated carbon supported type platinum catalyst or Karstedt type platinum catalyst.
4. antimicrobial compounds preparation method according to claim 1 is characterized in that, the described preparation method who contains the organo-siloxane of tertiary amine is: get (R
1O)
2R
2SiR
3X and R
4R
5NH under 20 ~ 80 ℃ of temperature, adds the NaOH/ aqueous isopropanol as catalyzer, and under agitation reacts duration 2 ~ 48h, and get final product; Wherein, R
1Be-CH
3Or-CH
2CH
3R
2Be-OR
1,-CH
3Or-CH
2CH
3R
3To be selected from-(CH
2)
p, p=1～10 wherein; R
4Be-(CH
2)
qCH
3, q=0～17 wherein; R
5Be-(CH
2)
qCH
3, q=0～17 wherein; X is Br, Cl or I.
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|---|---|---|---|
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103396550A (en) * | 2013-07-08 | 2013-11-20 | 上海师范大学 | Preparation method of imidazole functionalized amphiphilic periodic mesoporous organic silicon material |
| CN107447524A (en) * | 2017-08-11 | 2017-12-08 | 深圳市尼森实业有限公司 | A kind of synthetic method of environmental type textile antibacterial finish agent |
| CN112210341A (en) * | 2020-09-18 | 2021-01-12 | 山东东岳有机硅材料股份有限公司 | Double-vulcanization system building sealant and preparation method thereof |
| CN113529209A (en) * | 2021-07-15 | 2021-10-22 | 杭州逸腾新材料有限公司 | Superfine denier porous polyester yarn and preparation method thereof |
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| US5936703A (en) * | 1993-10-13 | 1999-08-10 | Nof Corporation | Alkoxysilane compound, surface processing solution and contact lens |
| US20090202816A1 (en) * | 2006-06-06 | 2009-08-13 | Florida State University Research Foundation, Inc. | Stabilized silica colloid |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103396550A (en) * | 2013-07-08 | 2013-11-20 | 上海师范大学 | Preparation method of imidazole functionalized amphiphilic periodic mesoporous organic silicon material |
| CN103396550B (en) * | 2013-07-08 | 2015-11-18 | 上海师范大学 | A kind of preparation method of the order mesoporous organosilicon material of amphiphilic of imidazoles functionalization |
| CN107447524A (en) * | 2017-08-11 | 2017-12-08 | 深圳市尼森实业有限公司 | A kind of synthetic method of environmental type textile antibacterial finish agent |
| CN112210341A (en) * | 2020-09-18 | 2021-01-12 | 山东东岳有机硅材料股份有限公司 | Double-vulcanization system building sealant and preparation method thereof |
| CN113529209A (en) * | 2021-07-15 | 2021-10-22 | 杭州逸腾新材料有限公司 | Superfine denier porous polyester yarn and preparation method thereof |
| CN113529209B (en) * | 2021-07-15 | 2023-01-03 | 杭州逸腾新材料有限公司 | Superfine denier porous polyester yarn and preparation method thereof |
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|---|---|
| CN102924496B (en) | 2015-04-22 |
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